CN103339141B - 作为hiv成熟抑制剂的c-3修饰的桦木酸衍生物的c-28胺 - Google Patents
作为hiv成熟抑制剂的c-3修饰的桦木酸衍生物的c-28胺 Download PDFInfo
- Publication number
- CN103339141B CN103339141B CN201280007020.0A CN201280007020A CN103339141B CN 103339141 B CN103339141 B CN 103339141B CN 201280007020 A CN201280007020 A CN 201280007020A CN 103339141 B CN103339141 B CN 103339141B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- octahydro
- pentamethyl
- prop
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 CN(CC*)C=C*=C Chemical compound CN(CC*)C=C*=C 0.000 description 11
- QSYTWBKZNNEKPN-UHFFFAOYSA-N CC(C)(C)OC(N1CCN(CCN)CC1)=O Chemical compound CC(C)(C)OC(N1CCN(CCN)CC1)=O QSYTWBKZNNEKPN-UHFFFAOYSA-N 0.000 description 1
- ROOIZNDAYDABMA-GXYXSIBPSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CNCCNC(C)=C)CC2 Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CNCCNC(C)=C)CC2 ROOIZNDAYDABMA-GXYXSIBPSA-N 0.000 description 1
- WSAXXWRZQRYWGS-UHFFFAOYSA-N CC(CCN(CC1)CC[S]1(=O)#N)CN Chemical compound CC(CCN(CC1)CC[S]1(=O)#N)CN WSAXXWRZQRYWGS-UHFFFAOYSA-N 0.000 description 1
- LNWWQYYLZVZXKS-UHFFFAOYSA-N CC(N1CCCC1)=O Chemical compound CC(N1CCCC1)=O LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 1
- HSQJBCLGDNMSNL-UHFFFAOYSA-N CC(O)S1CCN(CCCNCC(CCC2C(C)=C)(CC3)C2C(CC2)C3(C)C(C)(CC3)C2C2(C)C3C(C)(C)C(c(cc3)ccc3C(O)=O)=CC2)CC1 Chemical compound CC(O)S1CCN(CCCNCC(CCC2C(C)=C)(CC3)C2C(CC2)C3(C)C(C)(CC3)C2C2(C)C3C(C)(C)C(c(cc3)ccc3C(O)=O)=CC2)CC1 HSQJBCLGDNMSNL-UHFFFAOYSA-N 0.000 description 1
- CWLYJNKEQIWEIF-HWTGJUDZSA-N CC1(C)C(c(cc2)ccc2C(O)=O)=CC[C@](C)([C@@H](CC2)[C@@](C)(CC3)[C@@]4(C)C2(C)[C@@H]([C@@H](CC2)C(C)=C)[C@@]2(CNCCN(CCO)CCO)CC4)[C@]13N=C Chemical compound CC1(C)C(c(cc2)ccc2C(O)=O)=CC[C@](C)([C@@H](CC2)[C@@](C)(CC3)[C@@]4(C)C2(C)[C@@H]([C@@H](CC2)C(C)=C)[C@@]2(CNCCN(CCO)CCO)CC4)[C@]13N=C CWLYJNKEQIWEIF-HWTGJUDZSA-N 0.000 description 1
- LBNPEISQJLONDM-BTJQGHSGSA-N CCC(C)(CC1)[C@H]([C@H]2CC3)C1(CN(C)C)CC[C@@]2(C)[C@](C)(CC[C@H]1C(C)(C)C(C(CC2)=CC=C2C(O)=O)=CCC[C@@]11C)[C@]31N Chemical compound CCC(C)(CC1)[C@H]([C@H]2CC3)C1(CN(C)C)CC[C@@]2(C)[C@](C)(CC[C@H]1C(C)(C)C(C(CC2)=CC=C2C(O)=O)=CCC[C@@]11C)[C@]31N LBNPEISQJLONDM-BTJQGHSGSA-N 0.000 description 1
- GAKMLHBPAGIWBO-UHFFFAOYSA-N CCOC(CN)/[O]=C/C Chemical compound CCOC(CN)/[O]=C/C GAKMLHBPAGIWBO-UHFFFAOYSA-N 0.000 description 1
- QMHAHUAQAJVBIW-UHFFFAOYSA-N CN(C)S(N)(=O)=O Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 description 1
- SUMNGSPPKFDRTP-GXXIKKGZSA-N C[C@@H]1[C@](CC[C@](C)(CCC2)[C@](C)(CC3)C2[C@]2(C)[C@@H]3C(C)(C)C(c(cc3)cc(F)c3C(O)=O)=CC2)(CNCCCN(CCC2)C2=O)CCC1 Chemical compound C[C@@H]1[C@](CC[C@](C)(CCC2)[C@](C)(CC3)C2[C@]2(C)[C@@H]3C(C)(C)C(c(cc3)cc(F)c3C(O)=O)=CC2)(CNCCCN(CCC2)C2=O)CCC1 SUMNGSPPKFDRTP-GXXIKKGZSA-N 0.000 description 1
- DFWOXJWEBGETJF-UHFFFAOYSA-N C[I](CCCN)NC=[IH] Chemical compound C[I](CCCN)NC=[IH] DFWOXJWEBGETJF-UHFFFAOYSA-N 0.000 description 1
- WVFZXCIIJBHBAA-UHFFFAOYSA-N NCCC(N1CCOCC1)=O Chemical compound NCCC(N1CCOCC1)=O WVFZXCIIJBHBAA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437870P | 2011-01-31 | 2011-01-31 | |
| US61/437870 | 2011-01-31 | ||
| US61/437,870 | 2011-01-31 | ||
| PCT/US2012/022847 WO2012106188A1 (en) | 2011-01-31 | 2012-01-27 | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103339141A CN103339141A (zh) | 2013-10-02 |
| CN103339141B true CN103339141B (zh) | 2016-08-24 |
Family
ID=45567146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280007020.0A Expired - Fee Related CN103339141B (zh) | 2011-01-31 | 2012-01-27 | 作为hiv成熟抑制剂的c-3修饰的桦木酸衍生物的c-28胺 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8748415B2 (https=) |
| EP (1) | EP2670764B1 (https=) |
| JP (1) | JP6000283B2 (https=) |
| CN (1) | CN103339141B (https=) |
| BR (1) | BR112014010105A2 (https=) |
| CA (1) | CA2826257A1 (https=) |
| CY (1) | CY1116989T1 (https=) |
| DK (1) | DK2670764T3 (https=) |
| EA (1) | EA023578B1 (https=) |
| ES (1) | ES2552512T3 (https=) |
| HR (1) | HRP20151212T1 (https=) |
| HU (1) | HUE026371T2 (https=) |
| MX (1) | MX2013008359A (https=) |
| PL (1) | PL2670764T3 (https=) |
| PT (1) | PT2670764E (https=) |
| RS (1) | RS54352B1 (https=) |
| SI (1) | SI2670764T1 (https=) |
| SM (1) | SMT201500303B (https=) |
| WO (1) | WO2012106188A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2014002936A (es) | 2011-09-21 | 2014-04-25 | Bristol Myers Squibb Co | Nuevos derivados de acido betulinico con actividad antiviral. |
| US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| RU2519133C1 (ru) * | 2012-11-09 | 2014-06-10 | Леонид Леонидович Клопотенко | Мазь, содержащая инкапсулированную тритерпеновую кислоту или ее производные |
| RU2516952C1 (ru) * | 2012-11-09 | 2014-05-20 | Леонид Леонидович Клопотенко | Фармацевтическая композиция, содержащая инкапсулированную тритерпеновую кислоту или ее производные |
| CN103214543B (zh) * | 2012-12-25 | 2015-09-02 | 中国人民解放军海军医学研究所 | 新山楂酸衍生物、其制备方法及其在抗肿瘤药物中的应用 |
| JP6186010B2 (ja) | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| KR20150121712A (ko) * | 2013-02-25 | 2015-10-29 | 브리스톨-마이어스 스큅 컴퍼니 | Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체 |
| UY36070A (es) | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| WO2015195776A1 (en) * | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| CN107250152A (zh) | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | C17‑芳基取代的桦木酸类似物 |
| US9969767B2 (en) | 2014-11-14 | 2018-05-15 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| AU2015346314B2 (en) * | 2014-11-14 | 2018-04-12 | VIIV Healthcare UK (No.5) Limited | Extended betulinic acid analogs |
| EP3283467A1 (en) * | 2015-04-14 | 2018-02-21 | VIIV Healthcare UK(No.4) Limited | Methods of producing an hiv maturation inhibitor |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| KR20180054826A (ko) | 2015-09-24 | 2018-05-24 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 성숙 억제 활성을 갖는 화합물 |
| EP3405474A1 (en) | 2016-01-20 | 2018-11-28 | Glaxosmithkline Intellectual Property (No. 2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| EP3478703A1 (en) * | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| IL273078B2 (en) | 2017-09-13 | 2025-06-01 | Emmyon Inc | Ursolic acid morpholine and diethanolamine salts |
| MX2020002884A (es) | 2017-09-14 | 2020-10-05 | Phoenix Biotechnology Inc | Método y composición neuroprotectora mejorada para tratar afecciones neurológicas. |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US10343997B1 (en) | 2018-12-04 | 2019-07-09 | King Saud University | Ursolic acid derivatives |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| KR20220151038A (ko) | 2020-03-31 | 2022-11-11 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 예방를 위한 조성물 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101142227A (zh) * | 2004-11-12 | 2008-03-12 | 帕纳克斯医药公司 | 新颖的桦木醇衍生物、其制备和其用途 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| CA2714049A1 (en) * | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| RS54239B1 (sr) * | 2010-06-04 | 2015-12-31 | Bristol-Myers Squibb Company | C-28 amidi modifikovanih derivata c-3 betulinske kiseline kao inhibitori sazrevanja hiv-a |
| US8754068B2 (en) * | 2010-06-04 | 2014-06-17 | Bristol-Myers Squibb Company | Modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| US8846647B2 (en) * | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
-
2012
- 2012-01-27 HU HUE12702946A patent/HUE026371T2/en unknown
- 2012-01-27 DK DK12702946.0T patent/DK2670764T3/en active
- 2012-01-27 WO PCT/US2012/022847 patent/WO2012106188A1/en not_active Ceased
- 2012-01-27 JP JP2013551360A patent/JP6000283B2/ja not_active Expired - Fee Related
- 2012-01-27 CN CN201280007020.0A patent/CN103339141B/zh not_active Expired - Fee Related
- 2012-01-27 US US13/359,680 patent/US8748415B2/en not_active Expired - Fee Related
- 2012-01-27 ES ES12702946.0T patent/ES2552512T3/es active Active
- 2012-01-27 HR HRP20151212TT patent/HRP20151212T1/hr unknown
- 2012-01-27 EP EP12702946.0A patent/EP2670764B1/en active Active
- 2012-01-27 BR BR112014010105A patent/BR112014010105A2/pt unknown
- 2012-01-27 SI SI201230354T patent/SI2670764T1/sl unknown
- 2012-01-27 PL PL12702946T patent/PL2670764T3/pl unknown
- 2012-01-27 CA CA2826257A patent/CA2826257A1/en not_active Abandoned
- 2012-01-27 EA EA201391098A patent/EA023578B1/ru not_active IP Right Cessation
- 2012-01-27 PT PT127029460T patent/PT2670764E/pt unknown
- 2012-01-27 RS RS20150740A patent/RS54352B1/sr unknown
- 2012-01-27 MX MX2013008359A patent/MX2013008359A/es active IP Right Grant
-
2015
- 2015-12-01 SM SM201500303T patent/SMT201500303B/it unknown
- 2015-12-01 CY CY20151101099T patent/CY1116989T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101142227A (zh) * | 2004-11-12 | 2008-03-12 | 帕纳克斯医药公司 | 新颖的桦木醇衍生物、其制备和其用途 |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis and Anti-HIV Activity of Oleanolic Acid Derivatives;Yong-Ming Zhu,等;《Bioorganic & Medicinal Chemistry Letters》;20011231;第11卷;3115-3118 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL2670764T3 (pl) | 2016-02-29 |
| SMT201500303B (it) | 2016-01-08 |
| CN103339141A (zh) | 2013-10-02 |
| PT2670764E (pt) | 2015-11-20 |
| HRP20151212T1 (hr) | 2015-12-04 |
| JP2014507422A (ja) | 2014-03-27 |
| ES2552512T3 (es) | 2015-11-30 |
| US8748415B2 (en) | 2014-06-10 |
| BR112014010105A2 (pt) | 2017-06-13 |
| CA2826257A1 (en) | 2012-08-09 |
| WO2012106188A1 (en) | 2012-08-09 |
| HUE026371T2 (en) | 2016-05-30 |
| JP6000283B2 (ja) | 2016-09-28 |
| DK2670764T3 (en) | 2015-12-07 |
| EP2670764B1 (en) | 2015-09-02 |
| RS54352B1 (sr) | 2016-02-29 |
| MX2013008359A (es) | 2013-08-27 |
| US20130029954A1 (en) | 2013-01-31 |
| CY1116989T1 (el) | 2017-04-05 |
| EA201391098A1 (ru) | 2013-12-30 |
| SI2670764T1 (sl) | 2016-03-31 |
| EP2670764A1 (en) | 2013-12-11 |
| EA023578B1 (ru) | 2016-06-30 |
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